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WO2007047073A2 - Article composite et procede de fabrication associe faisant appel a un liant se presentant sous la forme d'un prepolymere a terminaison isocyanate - Google Patents

Article composite et procede de fabrication associe faisant appel a un liant se presentant sous la forme d'un prepolymere a terminaison isocyanate Download PDF

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Publication number
WO2007047073A2
WO2007047073A2 PCT/US2006/038280 US2006038280W WO2007047073A2 WO 2007047073 A2 WO2007047073 A2 WO 2007047073A2 US 2006038280 W US2006038280 W US 2006038280W WO 2007047073 A2 WO2007047073 A2 WO 2007047073A2
Authority
WO
WIPO (PCT)
Prior art keywords
composite article
binder
formula
urethane
particulate
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/US2006/038280
Other languages
English (en)
Other versions
WO2007047073A3 (fr
Inventor
Philippe Poncet
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Dow Global Technologies LLC
Original Assignee
Dow Global Technologies LLC
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Dow Global Technologies LLC filed Critical Dow Global Technologies LLC
Priority to AT06825292T priority Critical patent/ATE491742T1/de
Priority to JP2008535557A priority patent/JP5118049B2/ja
Priority to DK06825292.3T priority patent/DK1940931T3/da
Priority to PL06825292T priority patent/PL1940931T3/pl
Priority to BRPI0618405-7A priority patent/BRPI0618405B1/pt
Priority to EP06825292A priority patent/EP1940931B1/fr
Priority to CN200680038271XA priority patent/CN101287783B/zh
Priority to CA2625465A priority patent/CA2625465C/fr
Priority to DE602006018975T priority patent/DE602006018975D1/de
Publication of WO2007047073A2 publication Critical patent/WO2007047073A2/fr
Publication of WO2007047073A3 publication Critical patent/WO2007047073A3/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B25/00—Layered products comprising a layer of natural or synthetic rubber
    • B32B25/10—Layered products comprising a layer of natural or synthetic rubber next to a fibrous or filamentary layer
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B5/00—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts
    • B32B5/18—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts characterised by features of a layer of foamed material
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
    • C08G18/4804—Two or more polyethers of different physical or chemical nature
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
    • C08G18/4804—Two or more polyethers of different physical or chemical nature
    • C08G18/482—Mixtures of polyethers containing at least one polyether containing nitrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
    • C08G18/4829—Polyethers containing at least three hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
    • C08G18/4833—Polyethers containing oxyethylene units
    • C08G18/4837—Polyethers containing oxyethylene units and other oxyalkylene units
    • C08G18/4841—Polyethers containing oxyethylene units and other oxyalkylene units containing oxyethylene end groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
    • C08G18/50—Polyethers having heteroatoms other than oxygen
    • C08G18/5021—Polyethers having heteroatoms other than oxygen having nitrogen
    • C08G18/5024—Polyethers having heteroatoms other than oxygen having nitrogen containing primary and/or secondary amino groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/721—Two or more polyisocyanates not provided for in one single group C08G18/73 - C08G18/80
    • C08G18/725—Combination of polyisocyanates of C08G18/78 with other polyisocyanates
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
    • C08G18/78—Nitrogen
    • C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
    • C08G18/791—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
    • C08G18/78—Nitrogen
    • C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
    • C08G18/797—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing carbodiimide and/or uretone-imine groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L19/00—Compositions of rubbers not provided for in groups C08L7/00 - C08L17/00
    • C08L19/003—Precrosslinked rubber; Scrap rubber; Used vulcanised rubber
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
    • C08L75/04—Polyurethanes
    • C08L75/08—Polyurethanes from polyethers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
    • C08L75/04—Polyurethanes
    • C08L75/12—Polyurethanes from compounds containing nitrogen and active hydrogen, the nitrogen atom not being part of an isocyanate group
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L97/00—Compositions of lignin-containing materials
    • C08L97/007—Cork
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L97/00—Compositions of lignin-containing materials
    • C08L97/02—Lignocellulosic material, e.g. wood, straw or bagasse
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06N—WALL, FLOOR, OR LIKE COVERING MATERIALS, e.g. LINOLEUM, OILCLOTH, ARTIFICIAL LEATHER, ROOFING FELT, CONSISTING OF A FIBROUS WEB COATED WITH A LAYER OF MACROMOLECULAR MATERIAL; FLEXIBLE SHEET MATERIAL NOT OTHERWISE PROVIDED FOR
    • D06N7/00—Flexible sheet materials not otherwise provided for, e.g. textile threads, filaments, yarns or tow, glued on macromolecular material
    • D06N7/0063—Floor covering on textile basis comprising a fibrous top layer being coated at the back with at least one polymer layer, e.g. carpets, rugs, synthetic turf
    • D06N7/0071—Floor covering on textile basis comprising a fibrous top layer being coated at the back with at least one polymer layer, e.g. carpets, rugs, synthetic turf characterised by their backing, e.g. pre-coat, back coating, secondary backing, cushion backing
    • D06N7/0084—Floor covering on textile basis comprising a fibrous top layer being coated at the back with at least one polymer layer, e.g. carpets, rugs, synthetic turf characterised by their backing, e.g. pre-coat, back coating, secondary backing, cushion backing with at least one layer obtained by sintering or bonding granules together
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2264/00—Composition or properties of particles which form a particulate layer or are present as additives
    • B32B2264/02—Synthetic macromolecular particles
    • B32B2264/0207—Particles made of materials belonging to B32B25/00
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2264/00—Composition or properties of particles which form a particulate layer or are present as additives
    • B32B2264/02—Synthetic macromolecular particles
    • B32B2264/0214—Particles made of materials belonging to B32B27/00
    • B32B2264/0221—Thermoplastic elastomer particles
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2264/00—Composition or properties of particles which form a particulate layer or are present as additives
    • B32B2264/06—Vegetal particles
    • B32B2264/062—Cellulose particles, e.g. cotton
    • B32B2264/065—Lignocellulosic particles, e.g. jute, sisal, hemp, flax, bamboo
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2305/00—Condition, form or state of the layers or laminate
    • B32B2305/70—Scrap or recycled material
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2319/00—Synthetic rubber
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2371/00—Polyethers, e.g. PEEK, i.e. polyether-etherketone; PEK, i.e. polyetherketone
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2375/00—Polyureas; Polyurethanes
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2419/00—Buildings or parts thereof
    • B32B2419/04—Tiles for floors or walls
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2471/00—Floor coverings
    • B32B2471/04—Mats
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L25/00—Compositions of, homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring; Compositions of derivatives of such polymers
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06N—WALL, FLOOR, OR LIKE COVERING MATERIALS, e.g. LINOLEUM, OILCLOTH, ARTIFICIAL LEATHER, ROOFING FELT, CONSISTING OF A FIBROUS WEB COATED WITH A LAYER OF MACROMOLECULAR MATERIAL; FLEXIBLE SHEET MATERIAL NOT OTHERWISE PROVIDED FOR
    • D06N2203/00—Macromolecular materials of the coating layers
    • D06N2203/02—Natural macromolecular compounds or derivatives thereof
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06N—WALL, FLOOR, OR LIKE COVERING MATERIALS, e.g. LINOLEUM, OILCLOTH, ARTIFICIAL LEATHER, ROOFING FELT, CONSISTING OF A FIBROUS WEB COATED WITH A LAYER OF MACROMOLECULAR MATERIAL; FLEXIBLE SHEET MATERIAL NOT OTHERWISE PROVIDED FOR
    • D06N2203/00—Macromolecular materials of the coating layers
    • D06N2203/02—Natural macromolecular compounds or derivatives thereof
    • D06N2203/024—Polysaccharides or derivatives thereof
    • D06N2203/026—Cellulose or derivatives thereof
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06N—WALL, FLOOR, OR LIKE COVERING MATERIALS, e.g. LINOLEUM, OILCLOTH, ARTIFICIAL LEATHER, ROOFING FELT, CONSISTING OF A FIBROUS WEB COATED WITH A LAYER OF MACROMOLECULAR MATERIAL; FLEXIBLE SHEET MATERIAL NOT OTHERWISE PROVIDED FOR
    • D06N2203/00—Macromolecular materials of the coating layers
    • D06N2203/06—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06N2203/068—Polyurethanes
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06N—WALL, FLOOR, OR LIKE COVERING MATERIALS, e.g. LINOLEUM, OILCLOTH, ARTIFICIAL LEATHER, ROOFING FELT, CONSISTING OF A FIBROUS WEB COATED WITH A LAYER OF MACROMOLECULAR MATERIAL; FLEXIBLE SHEET MATERIAL NOT OTHERWISE PROVIDED FOR
    • D06N2205/00—Condition, form or state of the materials
    • D06N2205/10—Particulate form, e.g. powder, granule
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06N—WALL, FLOOR, OR LIKE COVERING MATERIALS, e.g. LINOLEUM, OILCLOTH, ARTIFICIAL LEATHER, ROOFING FELT, CONSISTING OF A FIBROUS WEB COATED WITH A LAYER OF MACROMOLECULAR MATERIAL; FLEXIBLE SHEET MATERIAL NOT OTHERWISE PROVIDED FOR
    • D06N2205/00—Condition, form or state of the materials
    • D06N2205/20—Cured materials, e.g. vulcanised, cross-linked

Definitions

  • the present invention relates to a composite article of a bound particulate substance; a method of its fabrication employing as binder a select urethane-modified isocyanate adhesive; and to a laminate product wherein one or more layers comprises such a composite product.
  • the composites based on known two-component polyurethane binders are obtained by mixing a polyisocyanate with a polyhydroxyl compound and compound simultaneously or subsequently with the particulate matter.
  • the polyisocyanate in addition reacts with the moisture from the atmosphere.
  • the proportions in which the two reactions take place depend, among other things, on the atmospheric humidity, and residual humidity within the particulate material, which affects the processing and end properties of the composite in a way which cannot easily be controlled.
  • This disadvantage is mitigated to some extent by using one-component polyurethane binders which are hardened only by their reaction with the atmospheric moisture. Alternatively, the disadvantage may also be mitigated to a limited extent by selection of urethane catalyst present in the process.
  • One component binders typically consist of prepolymers that contain isocyanate groups and having been obtained from reaction of usually polyhydroxyl compound(s) with a molar excess of a polyisocyanate.
  • the known one-component polyurethane binders have various disadvantages depending on their chemical structure and reactivity.
  • Prepolymers based on diphenylmethane-4,4'-diisocyanate have a tendency to crystallize at temperatures around 0 0 C or slightly above and, therefore have storage and use constraints in cold conditions.
  • Prepolymers based on commercial 5 diphenylmethane diisocyanate and which may additionally contain triisocyanates and tetraisocyanates as well as higher functional polyisocyanates of the diphenylmethane series have a much reduced tendency to crystallize, but on the other hand their viscosity at room temperature is so high that they are difficult to process without subsequent modification of their viscosity by the addition of thinners or solvents or o alternatively elevated processing temperatures.
  • the presence of solvents is not desirable as there is the risk that certain particulate matter may swell due to the absorption of solvent and subsequently be released in the curing process with potential to cause problems, for example, dimensional instability. Further increasing awareness of environmental concerns associated with volatile organic emissions make it desirable 5 to avoid the presence of such solvent.
  • alternative polyurethane binder system accommodating one or more desires of the end user for a system having easier processing, including cure times and sensitivity to humidity; fewer limitations associated with sensitivity to presence of solvents or catalysts; and enhanced mechanical performance.
  • the present invention relates to a composite article obtained from binding or adhesion of particulate matter with a polyurethane binder which is derived from a urethane-modified isocyanate obtained by reaction of an isocyanate with a polyether polyol derived from initiators containing a tertiary nitrogen.
  • Such composite articles can be, for example, recreational matting or tiles, sports or running tracks, or flooring, o or laminates.
  • this invention is a composite composed of particulate matter substantially coated with a non-foamed polyurethane binder based on a urethane- modified isocyanate characterized in that the urethane-modified isocyanate is the reaction product of: 5 a) a stoichiometric excess of an aliphatic or aromatic polyisocyanate, or mixtures thereof; with b) a polyol composition that comprises a polyether polyol (bl) having a molecular weight of from 1000 to 12000 and being obtained by alkoxylation of at least one o initiator molecule of the formula
  • n and p are independently integers from 2 to 6, 5 A at each occurrence is independently oxygen, nitrogen, sulphur or hydrogen, with the proviso that only one of A can be hydrogen at one time, R is a C 1 to C 3 alkyl group, m is equal to 0 when A is hydrogen, is 1 when A is oxygen and is 2 when A is nitrogen, or H 2 N-(CHaVN-(R)-H Formula (II) where t is an integer from 2 to 12 and R is a C 1 to C 3 alkyl group.
  • this invention is a process for manufacturing a composite comprising particulate matter substantially coated and bound together by a non-foamed polyurethane binder which comprises a first step of intimately contacting said particulate matter with a urethane-modified isocyanate composition and a subsequent step of permitting the resulting mixture to cure to give the composite article characterized in that the urethane-modified isocyanate is as described above.
  • this invention is a laminate article comprising a first layer being in contact with a second layer and wherein at least one of the first or second layers is a composite as mentioned herein above.
  • this invention relates to a mat with an upper tufted pile textile surface comprising tufts of yarn tufted into a substrate structure comprising an elastomeric backing derived from elastomeric crumbs and a polyurethane binder as mentioned hereinabove.
  • polyurethane binder comprising such urethane-modified isocyanate derived from a polyol based on the nitrogen containing initiator(s) permits reduction or even elimination of catalysts typically present to accelerate the curing of the polyurethane binder.
  • This has the advantage of offering systems that have reduced sensitivity to water or humidity content of the particulate matter thus avoiding susceptibility to foam formation. With such reduced water sensitivity; less time is required in drying and preparing the particulate matter for manufacture of the composite.
  • the ability to reduce or eliminate presence of curing catalysts means that such polyurethnae binders systems are now accessible to certain end applications previously excluded due to sensitivity associated with such catalyst substances.
  • Such composite article may be a compact article but in some instances, such as for example when being a laminate component of a mat, may be semi-compact article containing voids.
  • the composite article is a semi-compact article typically it will comprise from 50 to 95 percent by weight of particulate matter and from 5 to 95 percent by weight of the non-cellular polyurethane binder and wherein the void volume of the composite is from 15 to 85 percent by volume.
  • the particulate matter can be an inorganic or organic substance, or mixture thereof.
  • inorganic substances are sand, quartz, marble or other ground stone, ground glass, or a cementious material.
  • Composites based on inorganic matter such as sand can have utility in the foundry industry.
  • organic substances are elastomeric crumb of rubber or reground foam material, or a particulate ligno- cellulosic substance such as, for example, cork, wood, grass or straw.
  • the preferred particulate matter for the composite of this invention are organic substances including elastomeric rubbers, for example such as derived from styrene and butadiene, reground foam material or cork, and which optionally can be recovered/recycled materials.
  • Such particulate matter is eminently suitable for the manufacture of composites having utility as surfaces, sound absorbing materials and upper or under layers in recreational surfaces or pavement or roofing or flooring such as a mat, pad or tile for carpeting.
  • the average particle size in its longest dimension is less than about 20 mm, preferably less than about 15 mm and more preferably less than about 10 mm.
  • the average particles size is at least 1 mm, and preferably at least 3 mm in its longest dimension.
  • the polyol composition used in preparation of the urethane-modified o isocyanate may comprise one or more additional polyol(s) which are not initiated with an initiator containing a nitrogen atom.
  • additional polyol(s) are well known in the art and are described in such publications as High Polymers, Vol. XVI; "Polyurethanes, Chemistry and Technology", by Saunders and Frisch, hiterscience Publishers, New York, Vol. I, pp. 32-42, 44-54 (1962) and VoI II. Pp. 5-6, 198- 5 199 (1964); Organic Polymer Chemistry by K. J. Saunders, Chapman and Hall, London, pp. 323-325 (1973); and Developments in Polyurethanes, Vol.
  • polystyrene/acrylonitrile SAN
  • PIPA polyisocyanate polyaddition products
  • PPD polyurea polyols
  • the amount of polyol (bl) from the nitrogen-containing initiator present in the composition when preparing the urethane-modified isocyanate can be varied depending on degree of intrinsic reactivity required within the polyurethane binder systems for a given end application.
  • suitable compositions are when polyol (bl) is present in an amount of from 5 to 60, preferably from 5 to 50 and more preferably from 5 to 40 weight percent of the total weight of the polyol composition.
  • the remainder of the polyol is from non-nitrogen containing initiators and the total weight percent of polyol is 100.
  • Polyol (bl) used to prepare the urethane-modified isocyanate is a substance typically having an average molecular weight of from 1000 to l2000 Daltons, preferably from 1500 to 8000, and more preferably from 2000 to 6000 and is obtained by alkoxylation of an initiator comprising at least one molecule of the formula
  • n and p are independently integers from 2 to 6;
  • a at each occurrence is independently oxygen, nitrogen, sulphur or hydrogen, with the proviso that only one of A can be hydrogen at one time;
  • R is a C 1 to C 3 alkyl group; m is equal to 0 when A is hydrogen, m is 1 when A is oxygen and m is 2 when A is nitrogen,
  • R is methyl.
  • R is methyl and n and p are integers of the same value.
  • n and p are an integer of 2 to 4.
  • a at each occurrence will be either oxygen or nitrogen.
  • one A will be oxygen and the other A will be nitrogen, and the final polyol will be a triol.
  • A is nitrogen in all occurrences o and the final polyol will be a tetrol.
  • alkyl amines of Formula I are commercially available or can be made by techniques known in the art, such as U.S. Patent 4,605,772, the disclosure of which is incorporated herein by reference.
  • methylamine is reacted with the appropriate alkylene oxide for producing compounds where A is oxygen.
  • the alkylene oxide is ethylene oxide (EO), propylene oxide (PO), or butylene oxides
  • methyl amine can be o reacted with any known reactive group that reacts with an amine and contains additional nitrogen.
  • 2 moles of X(CH 2 ) n NR'R" can be reacted with one mole of methylamine where X represents chlorine, bromine or iodine; R 1 and R" can be H or an alkyl group; and n is as defined above.
  • examples of such initiator compounds include 3,3 '-diamino-N-methyldipropylamine, 2,2 '-diamino-N-methyldiethylamine, 5 2,3-diamino-N-methyl-ethyl-propylamine.
  • R is methyl.
  • Preferable t in Formula II is an o integer of 2 to 10, more preferably 2 to 6 and most preferred from 2 to 4.
  • R is methyl and m is an integer of 2 to 4.
  • Compounds of Formula II can be made by standard procedures known in the art. Examples of commercially available compounds of Formula II include N-methyl-l,2-ethanediamine and N-methyl-1,3- propanediamine. The production of polyols by alkoxylation of an initiator can be done by procedures well known in the art.
  • a polyol is made by the addition of an alkylene oxide (EO, PO, or BO), or a combination of alkylene oxides to the initiator by anionic or cationic reaction or use of double metal cyanide (DMC) catalyst.
  • EO alkylene oxide
  • PO polyethylene glycol
  • BO alkylene oxide
  • DMC double metal cyanide
  • the polyisocyanate reacted in excess with the above described polyol composition comprises an aliphatic polyisocyanate or an aromatic polyisocyanate, or mixtures thereof.
  • Suitable aliphatic polyisocyanates include hexamethylene diisocyanate and isophorone diisocyanate.
  • aromatic polyisocyanates including toluene diisocyanate, methylene diphenylisocyanate (MDI), including isomers thereof, and polymethylene polyphenylisocyanate (crude MDI).
  • the aromatic polyisocyanate is an isocyanate mixture that contains the 2-ring methylene diphenylisocyanate (MDI) isomers in at least about 40, preferably at least 50 and more preferably at least 60 weight percent of total isocyanate present.
  • MDI 2-ring methylene diphenylisocyanate
  • the MDI comprises the 2,4'- and 4,4 '-methylene diphenylisocyanate isomers in a molar ratio of from 10:90 to 90:10, preferably from 20:80 to 80:20, more preferably in from 20:80 to 70:30.
  • the balance of the isocyanate mixture when not methylene diphenylisocyanate can comprise toluene diisocyanate, hexamethylene diisocyanate, isophorone diisocyanate, polymethylene polyphenylisocyanate, carbodiimide or allophonate or uretonimine adducts of methylene diphenylisocyanate and mixtures thereof.
  • Preferred isocyanates to make up the balance of the composition are polymethylene polyphenylisocyanate, carbodiimide or allophonate or uretonimine adducts of methylene diphenylisocyanate.
  • the urethane-modified isocyanate is prepared in a conventional way by combining the isocyanate and the polyol at 20-100 0 C and if desired, in the presence of urethane-forming catalyst, such as a tertiary amine or tin compound.
  • urethane-forming catalyst such as a tertiary amine or tin compound.
  • the relative amounts of the isocyanate and the polyol are chosen in such a way as to arrive at the desired free NCO content of the final product.
  • the preparation of the prepolymer is a routine operation for those skilled in the art; see for example patent publication WO2004074343, incorporated herein by reference.
  • the present invention relates to a composite of particulate matter bound by a non-foamed polyurethane derived from the described urethane-modified isocyanate; and to laminate articles where one or more lamella can be composed of such a composite article. Methods of manufacturing such composite articles and laminates are extensively documented in the literature, incorporated herein by reference.
  • a process for manufacturing a composite being a particulate matter substantially coated and bound together by a non- foamed polyurethane binder comprises a first step of intimately contacting said particulate matter with a urethane- modified isocyanate composition and a subsequent step of permitting the resulting mixture to cure and give the composite article.
  • Ground rubber elastomeric composites useful in surfacings, sound absorbing materials, underlayers for recreational surfaces or other pavement or flooring can readily be prepared by coating the particulate matter, typically a ground vulcanized rubber with the polyurethane binder and bringing this mixture to a surface where it spread out and allowed to cure.
  • the urethane modified isocyanates of the present invention may also be used to prepare composites from inorganic particulate matter.
  • manufacture of artificial stone where quartz sand is bound using a polyurethane binder is disclosed in GB Patent 1,294,017.
  • Methods of manufacturing a mat with a textile surface, that can be composed of polypropylene fabric or tufted nylon or knitted polyester fabric or woven polyester; and an elastomer backing layer that includes elastomer crumbs, notably vulcanized rubber, and a polyurethane binder are disclosed in the following publications, incorporated herein by reference EP-A-1,518,668; EP-A-1511894; EP-A- 1,511,893; and EP-
  • Polyol A a glycerine EO/PO polyol having a hydroxyl equivalent weight of about 1700 available from The Dow Chemical Company as VORANOL 1421.
  • Polyol B a 4000 molecular weight diol based on propylene oxide with ethylene oxide capping available from The Dow Chemical Company as VORANOL EP 1900.
  • Polyisocyanate A A carbodiimide modified MDI available from The Dow
  • Polyisocyanate B A 50:50 weight blend of 2,4'- and 4,4'-MDI available from The Dow Chemical Company as ISONATE OP 50.
  • Polyisocyanate C A crude methylene diphenylisocyanate available from The Dow
  • Example 1 A polyurethane binder according to the present invention (Binder 1 or 2) is prepared and compared in performance to Binders A and B considered representative of the general state of the art.
  • the urethane-modified isocyanate compositions are prepared by reacting polyisocyanate with polyol as indicated below in Table I.
  • the obtained binders are then mixed with a styrene-butadiene particulate rubber in the presence of a small amount of residual water and optionally in the presence of an amine catalyst JEFFCAT DMDEE available from Huntsman Chemicals and the resulting mixture is trowelled into a mold held a temperature of about 90°C to give a tile having a thickness of 40 mm.
  • JEFFCAT DMDEE available from Huntsman Chemicals
  • Binders 1 and 2 provide an attractive open time and provide a drying time superior to Binders A and B; and noticeably in the absence of a curing catalyst.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Textile Engineering (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Laminated Bodies (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

La présente invention se rapporte à un article composite obtenu par la liaison ou l'adhésion d'une matière particulaire avec un liant polyuréthane qui est dérivé d'un isocyanate à modification uréthane, lequel est obtenu par la mise en réaction d'un isocyanate avec un polyol de polyéther à base d'un initiateur contenant un atome d'azote tertiaire. De tels articles composites peuvent par exemple se présenter sous la forme de dalles ou de tapis récréatifs, de pistes de sport ou de course à pied, de planchers ou de stratifiés.
PCT/US2006/038280 2005-10-14 2006-10-02 Article composite et procede de fabrication associe faisant appel a un liant se presentant sous la forme d'un prepolymere a terminaison isocyanate Ceased WO2007047073A2 (fr)

Priority Applications (9)

Application Number Priority Date Filing Date Title
AT06825292T ATE491742T1 (de) 2005-10-14 2006-10-02 Verbundgegenstand und herstellungsverfahren unter verwendung eines isocyanatterminierten prepolymers als bindemittel
JP2008535557A JP5118049B2 (ja) 2005-10-14 2006-10-02 結合剤としてイソシアネート終端プレポリマーを使用する複合品および製造方法
DK06825292.3T DK1940931T3 (da) 2005-10-14 2006-10-02 Kompositgenstand og fremgangsmåde til fremstilling heraf ved anvendelse af isocyanatafsluttet præpolymer som binder
PL06825292T PL1940931T3 (pl) 2005-10-14 2006-10-02 Wyrób kompozytowy i sposób jego wytwarzania z zastosowaniem prepolimeru zakończonego izocyjanianem jako spoiwa
BRPI0618405-7A BRPI0618405B1 (pt) 2005-10-14 2006-10-02 Artigo compósito, processo para fabricar um artigo compósito, artigo laminado, e tapete
EP06825292A EP1940931B1 (fr) 2005-10-14 2006-10-02 Article composite et procede de fabrication associe faisant appel a un liant se presentant sous la forme d'un prepolymere a terminaison isocyanate
CN200680038271XA CN101287783B (zh) 2005-10-14 2006-10-02 复合制品和使用异氰酸酯基封端的预聚物作为粘结剂的制备方法
CA2625465A CA2625465C (fr) 2005-10-14 2006-10-02 Article composite et procede de fabrication associe faisant appel a un liant se presentant sous la forme d'un prepolymere a terminaison isocyanate
DE602006018975T DE602006018975D1 (de) 2005-10-14 2006-10-02 Verbundgegenstand und herstellungsverfahren unter verwendung eines isocyanatterminierten prepolymers als bindemittel

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US60/726,897 2005-10-14

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JP5991476B2 (ja) * 2012-09-28 2016-09-14 セメダイン株式会社 物品の接着固定方法及びそれを用いた物品接着固定構造体
CN104530379B (zh) * 2014-12-19 2017-09-29 淄博正大聚氨酯有限公司 制作防水胶用单组分聚氨酯材料及其制备方法
JP6689858B2 (ja) * 2015-01-13 2020-04-28 ザ・シェファード・ケミカル・カンパニーＴｈｅ Ｓｈｅｐｈｅｒｄ Ｃｈｅｍｉｃａｌ Ｃｏｍｐａｎｙ 新規ポリウレタン硬化剤
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WO2011112813A1 (fr) * 2010-03-12 2011-09-15 Dow Global Technologies Llc Liants élastomères constitués de polyols à base d'huiles naturelles
US11312996B2 (en) 2010-05-18 2022-04-26 Natera, Inc. Methods for simultaneous amplification of target loci
WO2011147723A1 (fr) * 2010-05-27 2011-12-01 Basf Se Matériaux, leur procédé de fabrication et leurs composants
US8436125B2 (en) 2010-05-27 2013-05-07 Basf Se Materials, methods for production thereof and components thereof
US8853382B2 (en) 2010-08-05 2014-10-07 Hera Pharmaceuticals, Inc. Expression of antibody or a fragment thereof in lactobacillus
WO2013174970A1 (fr) 2012-05-24 2013-11-28 Henkel Ag & Co. Kgaa Corps moulé obtenus à partir de granulés et de colles polyuréthane bicomposantes, et contenant des isocyanates aliphatiques

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ATE491742T1 (de) 2011-01-15
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DE602006018975D1 (de) 2011-01-27
US20070088103A1 (en) 2007-04-19
WO2007047073A3 (fr) 2007-06-07
EP1940931B1 (fr) 2010-12-15
PL1940931T3 (pl) 2011-07-29
TW200728426A (en) 2007-08-01
BRPI0618405B1 (pt) 2018-01-02

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